Remote Sales Associate - Retail/Service Backgrounds Welcome!

Jerry; Richmond (VA); On-site; USD 26,000 - 29,000; Full time

Benefits offered by this job

License paid training

Remote work

Flexible schedule

Health, dental, vision & 401K matching

Equipment provided

Job summary

Jerry.ai is hiring for a full-time, remote inside sales role focused on insurance. You’ll complete paid training and licensing, guide users through the insurance purchase process, and help them compare 55+ insurers to fit their budget.

This position offers $19.00–$21.00 per hour with uncapped commissions, paid license costs, a fully remote setup with equipment provided, flexible scheduling, and comprehensive benefits including health, dental, vision, and 401(k) matching.

Responsibilities

• Go through (paid) training and insurance licensing (note: you must pass your licensing exam to legally sell insurance)
• Guide engaged users through the insurance purchasing process. There’s no cold-calling, these people have already started their insurance search in our app
• Simplify the Process: Help customers compare 55+ different insurance companies to find the one that fits their budget
• Solve Problems: Listen to a customer’s concerns and find a solution that makes them feel confident in their choice
• Close the Deal: Help customers finalize their new policy right then and there

Job description

Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all in one place. Since 2019, we’ve become one of the fastest-growing tech companies in the U.S.

This Role May Be a Fit For You If

• You know that people don’t just come to a place for the product, they come for the experience. You know how to make a customer feel welcome, taken care of, and will go above and beyond to give them an incredible experience.
• You’ve excelled in your retail job but are looking to transition into a long-term career with serious growth potential
• You’re self-motivated and would enjoy a remote environment. This role can be done 100% remotely (goodbye, sore feet at the end of a long day!)
• You thrive in a fast-paced & tech-focused environment: you’re used to handling several things at once while staying friendly. We’ll give you the best tools and tech to make that easy.

What You’ll Actually Do

• Go through (paid) training and insurance licensing (note: you must pass your licensing exam to legally sell insurance)
• Guide engaged users through the insurance purchasing process. There’s no cold-calling, these people have already started their insurance search in our app
• Simplify the Process: Help customers compare 55+ different insurance companies to find the one that fits their budget.
• Solve Problems: Listen to a customer’s concerns and find a solution that makes them feel confident in their choice.
• Close the Deal: Help customers finalize their new policy right then and there.

What’s in it for you?

• Pay: $19.00 - $21.00 per hour plus uncapped commission. *Our most successful team members typically earn $100,000+ per year.
• We Pay for Your License: Don't have an insurance license? No problem. We pay for your training and your exam (usually completed in your first two weeks).
• Work From Home: 100% remote. We provide all the equipment you need.
• Flexible Schedule: Choose between working five 8-hour days or four 10-hour days.
• Full Benefits: Medical, dental, vision insurance, and 401K matching.

This role includes flexible scheduling options, with the choice between a 5-day, 8-hour schedule or a 4-day, 10-hour workweek.

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at [e-mail]

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai

Your car and your home are your most expensive assets. And for most people, these aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair or, worse, an accident, and help you sell at the best price when the time is right. That friend is Jerry.

Jerry is building the first AI agent to manage all your physical assets. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace.

We've reached 5M+ customers, raised $240M+, and have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond.

We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.